JP2016138293A - 難燃性ウレタン樹脂組成物 - Google Patents
難燃性ウレタン樹脂組成物 Download PDFInfo
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- JP2016138293A JP2016138293A JP2016096184A JP2016096184A JP2016138293A JP 2016138293 A JP2016138293 A JP 2016138293A JP 2016096184 A JP2016096184 A JP 2016096184A JP 2016096184 A JP2016096184 A JP 2016096184A JP 2016138293 A JP2016138293 A JP 2016138293A
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- Prior art keywords
- urethane resin
- resin composition
- weight
- filler
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 229920002803 thermoplastic polyurethane Polymers 0.000 title claims abstract description 98
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 title claims abstract description 85
- 239000003063 flame retardant Substances 0.000 title claims abstract description 85
- 239000011342 resin composition Substances 0.000 title claims abstract description 77
- -1 polyol compound Chemical class 0.000 claims abstract description 53
- 239000000945 filler Substances 0.000 claims abstract description 46
- 229920005862 polyol Polymers 0.000 claims abstract description 42
- 239000003054 catalyst Substances 0.000 claims abstract description 26
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 25
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 25
- 239000000654 additive Substances 0.000 claims abstract description 22
- 239000002245 particle Substances 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 21
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims abstract description 15
- 238000010438 heat treatment Methods 0.000 claims abstract description 15
- 238000005829 trimerization reaction Methods 0.000 claims abstract description 14
- 238000002844 melting Methods 0.000 claims abstract description 8
- 230000008018 melting Effects 0.000 claims abstract description 8
- 230000000996 additive effect Effects 0.000 claims description 18
- 239000006260 foam Substances 0.000 claims description 18
- 239000004088 foaming agent Substances 0.000 claims description 14
- 239000003381 stabilizer Substances 0.000 claims description 13
- 238000005259 measurement Methods 0.000 claims description 10
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- 229910003475 inorganic filler Inorganic materials 0.000 claims description 8
- 238000010998 test method Methods 0.000 claims description 4
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- 229910019142 PO4 Inorganic materials 0.000 description 19
- 239000010452 phosphate Substances 0.000 description 19
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 239000000835 fiber Substances 0.000 description 11
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 10
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- 238000000034 method Methods 0.000 description 9
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- 238000001723 curing Methods 0.000 description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
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- 240000008042 Zea mays Species 0.000 description 7
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- 238000006243 chemical reaction Methods 0.000 description 7
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- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- 229910004298 SiO 2 Inorganic materials 0.000 description 5
- NJLLQSBAHIKGKF-UHFFFAOYSA-N dipotassium dioxido(oxo)titanium Chemical compound [K+].[K+].[O-][Ti]([O-])=O NJLLQSBAHIKGKF-UHFFFAOYSA-N 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 229960003742 phenol Drugs 0.000 description 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 4
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- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- MSSNHSVIGIHOJA-UHFFFAOYSA-N pentafluoropropane Chemical compound FC(F)CC(F)(F)F MSSNHSVIGIHOJA-UHFFFAOYSA-N 0.000 description 4
- 150000003014 phosphoric acid esters Chemical class 0.000 description 4
- 229920006389 polyphenyl polymer Polymers 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 3
- 229910018072 Al 2 O 3 Inorganic materials 0.000 description 3
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- 229910010413 TiO 2 Inorganic materials 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000004359 castor oil Substances 0.000 description 3
- 235000019438 castor oil Nutrition 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
- 230000014759 maintenance of location Effects 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 229920003986 novolac Polymers 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- GTRSAMFYSUBAGN-UHFFFAOYSA-N tris(2-chloropropyl) phosphate Chemical compound CC(Cl)COP(=O)(OCC(C)Cl)OCC(C)Cl GTRSAMFYSUBAGN-UHFFFAOYSA-N 0.000 description 3
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- GTEXIOINCJRBIO-UHFFFAOYSA-N 2-[2-(dimethylamino)ethoxy]-n,n-dimethylethanamine Chemical compound CN(C)CCOCCN(C)C GTEXIOINCJRBIO-UHFFFAOYSA-N 0.000 description 2
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
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- OJMOMXZKOWKUTA-UHFFFAOYSA-N aluminum;borate Chemical compound [Al+3].[O-]B([O-])[O-] OJMOMXZKOWKUTA-UHFFFAOYSA-N 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
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- BOSAWIQFTJIYIS-UHFFFAOYSA-N 1,1,1-trichloro-2,2,2-trifluoroethane Chemical compound FC(F)(F)C(Cl)(Cl)Cl BOSAWIQFTJIYIS-UHFFFAOYSA-N 0.000 description 1
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Classifications
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Abstract
【解決手段】 難燃性ウレタン樹脂組成物は、ポリイソシアネート化合物、ポリオール化合物、三量化触媒、発泡剤、および添加剤を含む難燃性ウレタン樹脂組成物であって、前記添加剤が赤リンと、フィラーとを含み、フィラーのアスペクト比が5〜50、平均粒径が0.1μm以上15μm未満、融点が750℃以上である。
【選択図】なし
Description
本願は、2014年9月26日に出願した特願2014-197047号明細書の優先権の利益を主張するものであり、当該明細書はその全体が参照により本明細書中に援用される。
(技術分野)
本発明は、難燃性ウレタン樹脂組成物に関する。
ここで、
イソシアネートの当量数=ポリイソシアネートの使用部数×NCO含有率(%)÷100/NCOの分子量、
ポリオールの当量数=OHV×ポリオールの使用部数÷KOHの分子量、OHVはポリオールの水酸基価(mg KOH/g)、
水の当量数=水の使用部数×水のOH基の数/水の分子量
である。なお上記式において、使用部数の単位は重量(g)であり、NCO基の分子量は42、NCO含有率はポリイソシアネート化合物中のNCO基の割合を質量%で表したものであり、
上記式の単位換算の都合上KOHの分子量は56100とし、水の分子量は18、水のOH基の数は2とする。
1.難燃性ウレタン樹脂組成物からなる発泡成形体の製造
表1及び表2に示した配合により、実施例1〜20及び比較例1〜14に係る難燃性ウレタン樹脂組成物をそれぞれ準備した。表中の各成分の詳細は次の通りである。
1.ポリオール化合物
(A-1) p−フタル酸ポリエステルポリオール(川崎化成工業社製、製品名:マキシモールRFK−505、水酸基価=250mgKOH/g)
(A-2) p−フタル酸ポリエステルポリオール(川崎化成工業社製、製品名:マキシモールRLK−087、水酸基価=200mgKOH/g)
2.触媒
(B-1)三量化触媒(オクチル酸カリウム、モメンティブ・パフォーマンス・マテリアルズ社製、製品名:K−Zero G)
(B-2)三量化触媒(東ソー社製、製品名:TOYOCAT−TR20)
(B-3)ウレタン化触媒(ペンタメチルジエチレントリアミン、東ソー社製、製品名:TOYOCAT−DT)
(B-4)三量化触媒(東ソー社製、製品名:TOYOCAT−RX5)
(B-5)ウレタン化触媒(トリエチレンジアミン、東ソー社製、製品名:TEDA−L33)
(B-6)ウレタン化触媒(1,2−ジメチルイミダゾール、東ソー社製、製品名:TOYOCAT−DM70)
ポリアルキレングリコール系整泡剤(東レダウコーニング社製、製品名:SH−193)
4.発泡剤
(C-1)純水
(C-2)HFC HFC−365mfc(1,1,1,3,3−ペンタフルオロブタン、日本ソルベイ社製)およびHFC−245fa(1,1,1,3,3−ペンタフルオロプロパン、セントラル硝子社製)、混合比率 HFC−365mfc:HFC−245fa = 7:3、以下「HFC」という)
5.イソシアネート化合物 (以下、「ポリイソシアネート」という)
MDI(日本ポリウレタン工業社製、製品名:ミリオネートMR−200)粘度:167mPa・s、NCO含有量=32.1%
6.添加剤
(D-1)赤リン(燐化学工業社製、製品名:ノーバエクセル140)
(D-2)トリス(β−クロロプロピル)ホスフェート(大八化学社製、製品名:TMCPP、以下「TMCPP」という。)
(D-3)臭素含有難燃剤(マナック社製、製品名:HBB−b、以下「HBB」という。)
(D-4)リン酸二水素アンモニウム(太平化学産業社製)
(E-1)ウォラストナイト(SiO2・CaO)(キンセイマテック社製、製品名:SH−1250)アスペクト比10〜16、平均粒径4.5〜6.5μm
(E-2)ウォラストナイト(SiO2・CaO)(キンセイマテック社製、製品名:SH−800)アスペクト比15〜20、平均粒径6〜9μm
(E-3)ウォラストナイト(SiO2・CaO)(キンセイマテック社製、製品名:SH−600)アスペクト比12〜18、平均粒径9.5〜13μm
(E-4)ウォラストナイト(SiO2・CaO)(キンセイマテック社製、製品名:SH−400)アスペクト比12〜18、平均粒径15〜25μm
(E-5)ウォラストナイト(SiO2・CaO)(キンセイマテック社製、製品名:FRW−800)アスペクト比2〜4、平均粒径3.5〜4.5μm
(E-6)チタン酸カリウムウィスカー(K2OnTiO2)(大塚化学社製、製品名:ティスモ D)アスペクト比17〜33、平均粒径0.3〜0.6μm
(E-7)チタン酸カリウムウィスカー(K2OnTiO2)(大塚化学社製、製品名:テラセス TF−S)平均粒径3〜11μm
(E-8)チタン酸カリウムウィスカー(K2OnTiO2)(大塚化学社製、製品名: テラセス JP)平均粒径6〜13μm
(E-9)アルミナ(Al2O3・H2O)(河合石灰工業社製、製品名: セラシュール BMI)アスペクト比30〜50、平均粒径4〜6μm
(E-10)アルミナ(Al2O3・H2O)(河合石灰工業社製、製品名: セラシュール BMF)アスペクト比40〜50、平均粒径3〜5μm
(E-11)アルミナ(Al2O3・H2O)(河合石灰工業社製、製品名: セラシュール BMM)アスペクト比10、平均粒径0.8〜1μm
下記の表1及び表2の配合に従い、ポリイソシアネート化合物、HFC成分を除くポリオール化合物、整泡剤、各種触媒、発泡剤、添加剤、及びフィラーを1000mLポリプロピレンビーカーにはかりとり、25℃、10秒間ハンドミキサーで撹拝した。撹拝後の混練物に対してポリイソシアネート化合物、HFC成分を加え、ハンドミキサーで約10秒間擾拝し発泡体を作成した。得られた難燃性ウレタン樹脂組成物は時間の経過と共に流動性を失い、実施例1〜20及び比較例1〜14の難燃性ウレタン樹脂組成物の発泡成形体を得た。
(総発熱量の測定)
硬化物から100mm×100mm×20mm(長さ方向×幅方向×厚み方向)になるようにコーンカロリーメーター試験用サンプルを切り出し、ISO−5660に準拠し、輻射熱強度50kW/m2にて20分間加熱した。結果を表1及び2に示す。
(密度の測定)
硬化物から100mm×100mm×20mm(長さ方向×幅方向×厚み方向)になるようにコーンカロリーメーター試験用サンプルを切り出し、ノギスを使用して寸法を計測し、電子天びんで質量を計測し密度を測定した。結果を表1及び2に示す。
(収縮測定)
上記のコーンカロリーメーター試験で加熱したときの収縮量及び変形量(mm)を測定した。図1(a)に示されるように、Xは長さ方向、Yは幅方向、図1(b)に示されるように、Zは厚み方向を示す。試験用サンプルをX方向,Y方向で3点ずつ測定し、Z方向は最も収縮した箇所で測定し、いずれの方向も最も収縮した数値を採用した。長さ方向及び幅方向の成形体の長さが95mmより大きい場合に合格、95mm以下を不合格とし、厚み方向の変形が10mm未満を合格、10mm以上を不合格とし、X,Y,Z方向のすべての方向で合格の場合を○と判定し、X,Y,Z方向の少なくとも一つの方向で不合格の場合を×と判定した。結果を表1及び2に示す。
実施例1で用いた各フィラーをウレタン樹脂100重量部に対し、3重量部、6重量部、又は9重量部とした以外は、実施例1と同じ材料及び配合で発泡成形体を製造した。各フィラーの粒径はX線透過式沈降法粒度分布測定装置で求め、アスペクト比を測定した。
Claims (6)
- ポリイソシアネート化合物、ポリオール化合物、三量化触媒、発泡剤、整泡剤、添加剤、およびフィラーを含む難燃性ウレタン樹脂組成物であって、前記添加剤が赤リンを含み、該フィラーのアスペクト比が5〜50、平均粒径が0.1μm以上15μm未満、融点が750℃以上であることを特徴とする難燃性ウレタン樹脂組成物。
- 空気条件下でのTG/DTA測定における前記フィラーの重量減少率が5%以下である請求項1に記載の難燃性ウレタン樹脂組成物。
- 前記フィラーは針状の無機フィラーである請求項1又は2に記載の難燃性ウレタン樹脂組成物。
- 前記ポリイソシアネート化合物および前記ポリオール化合物からなるウレタン樹脂100重量部を基準として、前記赤リンが3.5〜30重量部、前記フィラーが3〜30重量部である請求項1〜3のいずれか一項に記載の難燃性ウレタン樹脂組成物。
- 請求項1〜4のいずれか一項に記載の難燃性ウレタン樹脂組成物からなる成形体。
- 100mm×100mm×20mmの前記成形体をISO−5660試験方法に従って輻射熱強度50kW/m2にて20分間加熱したときの加熱前に対する加熱後の成形体の長さ方向及び幅方向の寸法が95mmよりも大きく、厚み方向の変形が10mm未満である請求項5に記載の成形体。
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US11236192B2 (en) | 2015-09-30 | 2022-02-01 | Sekisui Chemical Co., Ltd. | Flame-retardant rigid polyurethane foam |
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JP6134421B2 (ja) | 2017-05-24 |
WO2016047767A1 (ja) | 2016-03-31 |
KR20170060009A (ko) | 2017-05-31 |
US20170298170A1 (en) | 2017-10-19 |
JP5986693B2 (ja) | 2016-09-06 |
JPWO2016047767A1 (ja) | 2017-04-27 |
CN106715589A (zh) | 2017-05-24 |
EP3199590A4 (en) | 2018-04-25 |
TW201619289A (zh) | 2016-06-01 |
EP3199590A1 (en) | 2017-08-02 |
CN106715589B (zh) | 2021-05-11 |
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US10633480B2 (en) | 2020-04-28 |
KR102156004B1 (ko) | 2020-09-15 |
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